TY - JOUR
T1 - Switchable product selectivity in dehydration of N-acetyl-D-glucosamine promoted by choline chloride-based deep eutectic solvents
AU - Zhao, Jiancheng
AU - Pedersen, Christian Marcus
AU - Chang, Honghong
AU - Hou, Xianglin
AU - Wang, Yingxiong
AU - Qiao, Yan
N1 - Funding Information:
The authors thank for National Natural Science Foundation of China ( 22075308 ) and Natural Science Foundation of Shanxi Province ( 202103021224439 ) for financial support.
Publisher Copyright:
© 2023 The Author(s)
PY - 2023/7/21
Y1 - 2023/7/21
N2 - Herein, we report choline chloride-based deep eutectic solvents (DESs) promoted conversion of N-acetyl-D-glucosamine (GlcNAc) into nitrogen-containing compounds, i.e., 3-acetamido-5-(1′,2′-dihydroxyethyl) furan (Chromogen III) and 3-acetamido-5-acetylfuran (3A5AF). The binary deep eutectic solvent choline chloride-glycerin (ChCl-Gly), was found to promote the dehydration of GlcNAc to form Chromogen III, which reaches a maximum yield of 31.1%. On the other hand, the ternary deep eutectic solvent, choline chloride-glycerol-B(OH)3 (ChCl-Gly-B(OH)3), promoted the further dehydration of GlcNAc into 3A5AF with a maximum yield of 39.2%. In addition, the reaction intermediate, 2-acetamido-2,3-dideoxy-D-erythro-hex-2-enofuranose (Chromogen I), was detected by in situ nuclear magnetic resonance (NMR) techniques when promoted by ChCl-Gly-B(OH)3. The experimental results of the 1H NMR chemical shift titration showed ChCl-Gly interactions with α-OH-3 and α-OH-4 of GlcNAc, which is responsible for promoting the dehydration reaction. Meanwhile, the strong interaction between Cl− and GlcNAc was demonstrated by 35Cl NMR.
AB - Herein, we report choline chloride-based deep eutectic solvents (DESs) promoted conversion of N-acetyl-D-glucosamine (GlcNAc) into nitrogen-containing compounds, i.e., 3-acetamido-5-(1′,2′-dihydroxyethyl) furan (Chromogen III) and 3-acetamido-5-acetylfuran (3A5AF). The binary deep eutectic solvent choline chloride-glycerin (ChCl-Gly), was found to promote the dehydration of GlcNAc to form Chromogen III, which reaches a maximum yield of 31.1%. On the other hand, the ternary deep eutectic solvent, choline chloride-glycerol-B(OH)3 (ChCl-Gly-B(OH)3), promoted the further dehydration of GlcNAc into 3A5AF with a maximum yield of 39.2%. In addition, the reaction intermediate, 2-acetamido-2,3-dideoxy-D-erythro-hex-2-enofuranose (Chromogen I), was detected by in situ nuclear magnetic resonance (NMR) techniques when promoted by ChCl-Gly-B(OH)3. The experimental results of the 1H NMR chemical shift titration showed ChCl-Gly interactions with α-OH-3 and α-OH-4 of GlcNAc, which is responsible for promoting the dehydration reaction. Meanwhile, the strong interaction between Cl− and GlcNAc was demonstrated by 35Cl NMR.
KW - Green chemistry
KW - Organic chemistry
U2 - 10.1016/j.isci.2023.106980
DO - 10.1016/j.isci.2023.106980
M3 - Journal article
C2 - 37332676
AN - SCOPUS:85161716973
SN - 2589-0042
VL - 26
JO - iScience
JF - iScience
IS - 7
M1 - 106980
ER -